(S)-tert-butyl 4-((R,2E,4E)-1-hydroxyhexadeca-2,4-dien-1-yl)-2,2-dimethyloxazolidine-3-carboxylate | 410082-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-tert-butyl 4-((R,2E,4E)-1-hydroxyhexadeca-2,4-dien-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: N-tert-butoxycarbonyl (4S)-4-[1'-hydroxy-(2'E,4'E)-hexadecadienyl]-2,2-dimethyl-1,3-oxazolidine；tert-butyl (4S)-4-[(1R,2E,4E)-1-hydroxyhexadeca-2,4-dienyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 410082-76-7
• 化学式: C₂₆H₄₇NO₄
• 分子量: 437.663
• InChiKey: MCFKPSMSSGDCRR-FCMUNLJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 4-((R,2E,4E)-1-hydroxyhexadeca-2,4-dien-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.0h， 生成 (2S,3R,4E,6E)-2-aminooctadeca-4,6-diene-1,3-diol
  参考文献：
  名称：

  Synthesis of New Trans Double-Bond Sphingolipid Analogues:  Δ^4,6 and Δ⁶ Ceramides

  摘要：

  Unsaturation was introduced at Delta(4.6) and Delta(6) of the sphingoid chain of naturally occurring ceramide 1 via a beta-keto sulfoxide (12) and sulfone (18) derived from N-Boe-L-serine methyl ester acetonide (9), affording two novel ceramide analogues, (2S,3R)-2-octanoylamidooetadeca-(4E,6E)-diene-1,3-diol (2) and (2S,3R)-2-octanoylamidooetadec-(6E)-ene-1,3-diol (3). After C-alkylation of 12 with (E)1-bromo-2-tetradecene (8), a trans double bond was installed by elimination of PhS(O)H, providing conjugated dienone oxazolidine 13. Reaction of 18 with 8, followed by desulfonation (AI(Hg)), afforded keto-oxazolidine 20, which bears a (E)-Delta(6) double bond. The syntheses of analogues 2 and 3 from ketones 13 and 20, respectively, were completed by the following sequence of reactions: diastereoselective reduction (NaBH4/CeCl3 or DIBAL-H), hydrolysis of the oxazolidine ring, liberation of the amino group, and installation of the N-amide group.

  DOI：

  10.1021/jo0162639
• 作为产物：
  描述：

  (S)-(-)-3-BOC-4-甲氧羰基-2,2-二甲基-1,3-恶唑烷 在 正丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二异丙胺 、 红铝 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 生成 (S)-tert-butyl 4-((R,2E,4E)-1-hydroxyhexadeca-2,4-dien-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of New Trans Double-Bond Sphingolipid Analogues:  Δ^4,6 and Δ⁶ Ceramides

  摘要：

  Unsaturation was introduced at Delta(4.6) and Delta(6) of the sphingoid chain of naturally occurring ceramide 1 via a beta-keto sulfoxide (12) and sulfone (18) derived from N-Boe-L-serine methyl ester acetonide (9), affording two novel ceramide analogues, (2S,3R)-2-octanoylamidooetadeca-(4E,6E)-diene-1,3-diol (2) and (2S,3R)-2-octanoylamidooetadec-(6E)-ene-1,3-diol (3). After C-alkylation of 12 with (E)1-bromo-2-tetradecene (8), a trans double bond was installed by elimination of PhS(O)H, providing conjugated dienone oxazolidine 13. Reaction of 18 with 8, followed by desulfonation (AI(Hg)), afforded keto-oxazolidine 20, which bears a (E)-Delta(6) double bond. The syntheses of analogues 2 and 3 from ketones 13 and 20, respectively, were completed by the following sequence of reactions: diastereoselective reduction (NaBH4/CeCl3 or DIBAL-H), hydrolysis of the oxazolidine ring, liberation of the amino group, and installation of the N-amide group.

  DOI：

  10.1021/jo0162639

文献信息

• From the configurational preference of dihydroceramide desaturase-1 towards Δ⁶-unsaturated substrates to the discovery of a new inhibitor
  作者：Ana Pou、José-Luís Abad、Yadira F. Ordóñez、Maria Garrido、Josefina Casas、Gemma Fabriàs、Antonio Delgado

  DOI：10.1039/c6cc08268h

  日期：——

  The configurational preference of Des1 towards a [capital Delta]6-unsaturated dihydroceramide analog unveils a potent Des1 inhibitor.

  DES1的朝向[资本德尔塔]的构型优选6不饱和的二氢类似物推出一种有效的DES1抑制剂。